Ozone Applications

Заиков, Г. Е.; Rakovsky, Slavcho; Anachkov, M.P.

doi:10.1002/0471238961.ozonzaik.a01

Cited by 3 publications

(2 citation statements)

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“…Step 2 is considered to be a very important reaction to produce four diastereomers on the cabbage leaf surface, in which the four patterns of nonhomologous random recombination of carbonyl oxide ions and carbonyl compounds produced from the primary ozonide may be deeply involved. Incidentally, the secondary ozonides are considered to be less toxic to mammals because they are highly likely to be unstable in mammalian tissue due to their rapid decomposition in aqueous solutions. − Furthermore, an ozonide derivative of unsaturated lipid, methyl oleate, was orally administered to rats, which resulted in low toxicity, probably due to its fast degradation by enzymes and biological antioxidants such as glutathione transferase and vitamins, respectively …”

Section: Discussionmentioning

confidence: 99%

Metabolism of the Insecticide Metofluthrin in Cabbage (Brassica oleracea)

Ando

Fukushima

Fujisawa

et al. 2012

J. Agric. Food Chem.

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The metabolic fate of metofluthrin [2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (E,Z)-(1R,3R)-2,2-dimethyl-3-(prop-1-enyl)cyclopropanecarboxylate] separately labeled with (14)C at the carbonyl carbon and the α-position of the 4-methoxymethylbenzyl ring was studied in cabbage ( Brassica oleracea ). An acetonitrile solution of (14)C-metofluthrin at 431 g ai ha(-1) was once applied topically to cabbage leaves at head-forming stage, and the plants were grown for up to 14 days. Each isomer of metofluthrin applied onto the leaf surface rapidly volatilized into the air and was scarcely translocated to the untreated portion. On the leaf surface, metofluthrin was primarily degraded through ozonolysis of the propenyl side chain to produce the secondary ozonide, which further decomposed to the corresponding aldehyde and carboxylic acid derivatives. In the leaf tissues, the 1R-trans-Z isomer was mainly metabolized to its dihydrodiol derivative probably via an epoxy intermediate followed by saccharide conjugation in parallel with the ester cleavage, whereas no specific metabolite was dominant for the 1R-trans-E isomer. Isomerization of metofluthrin at the cyclopropyl ring was negligible for both isomers. In this study, the chemical structure of each secondary ozonide derivative was fully elucidated by the various modes of liquid chromatography-mass spectrometry (LC-MS) and nuclear magnetic resonance (NMR) spectroscopy together with cochromatography with the synthetic standard, and their cis/trans configuration was examined by the nuclear Overhauser effect (NOE) difference NMR spectrum.

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Section: Discussionmentioning

confidence: 99%

Metabolism of the Insecticide Metofluthrin in Cabbage (Brassica oleracea)

Ando

Fukushima

Fujisawa

et al. 2012

J. Agric. Food Chem.

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“…Studies of anthropogenic and biogenic alkene ozonolysis in the atmosphere have concluded − that these reactions have a complex impact on air pollution and the overall composition of the atmosphere. Many of these studies cite the need for a more complete understanding of the mechanism of the ozone–alkene reaction. − The reaction mechanism first proposed by Criegee in 1949 , is widely accepted ,, on the basis of considerable indirect experimental evidence and theoretical calculations. − This mechanism begins with the formation of an initial primary ozonide through addition of the ozone across the double bond followed by C–C and O–O bond rupture to form a Criegee intermediate and a carbonyl-containing species. However, other mechanisms have been proposed .…”

Section: Introductionmentioning

confidence: 99%

Matrix Isolation Study of the Ozonolysis of 1,3- and 1,4-Cyclohexadiene: Identification of Novel Reaction Pathways

2013

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The ozonolysis reactions of 1,3- and 1,4-cyclohexadiene have been studied using a combination of matrix isolation, infrared spectroscopy, and theoretical calculations. Experimental and theoretical results demonstrate that these reactions predominantly do not follow the long-accepted Criegee mechanism. Rather, the reaction of O3 with 1,4-cyclohexadiene leads to the essentially barrierless formation of benzene, C6H6, and H2O3. These two species are then trapped in the same argon matrix cage and weakly interact to form a molecular complex. There is also evidence for the formation of a small amount of the primary ozonide as a minor product, formed through a transition state that is slightly higher in energy. The reaction of O3 with 1,3-cyclohexadiene follows two pathways, one of which is the Criegee mechanism through a low energy transition state leading to formation of the primary ozonide. In addition, with a similar barrier, ozone abstracts a single hydrogen from C5 while adding to C1, forming a hydroperoxy intermediate. This study presents two of the rare cases in which the Criegee mechanism is not the dominant pathway for the ozonolysis of an alkene as well as the first evidence for dehydrogenation of an alkene by ozone.

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Ozone

Kirschner¹

2000

Ullmann's Encyclopedia of Industrial Chemistry

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The article contains sections titled: 1. Introduction 2. Physical Properties 3. Chemical Properties 4. Production 5. Environmental Protection 6. Analysis 7. Uses 7.1. Potable Water Filtration and Disinfection 7.2. Wastewater Treatment 7.3. Other Uses 8. Toxicology and Occupational Health

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Ozone Applications

Cited by 3 publications

References 100 publications

Metabolism of the Insecticide Metofluthrin in Cabbage (Brassica oleracea)

Metabolism of the Insecticide Metofluthrin in Cabbage (Brassica oleracea)

Matrix Isolation Study of the Ozonolysis of 1,3- and 1,4-Cyclohexadiene: Identification of Novel Reaction Pathways

Ozone

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